Thioacetamide → 7-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

HRID 2422519Notes

Reaction equation

HRID 2422519 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13](=O)[CH2:14]Br)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[C:17]([NH2:20])(=[S:19])[CH3:18]>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[N:20]=[C:17]([CH3:18])[S:19][CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

Product 1

HCID 598148377-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-bromo-4-(bromoacetyl)-2H-chromen-2-one (1.45 g, 4.19 mmol) in N,N-dimethylformamide (12.5 mL), thioacetamide (346 mg, 4.6 mmol) was added. The reaction was then stirred overnight at 100° C. After cooling, the reaction mixture was dissolved with a 4:1 mixture of CH2Cl2/hexanes. The mixture obtained was washed (3×) with water and the organic layer was concentrated under reduced pressure. The solid obtained was swished in a 4:1 mixture of hexanes/EtOAc. The solid obtained was collected by filtration and used as such for the next step. 1H NMR (400 MHz, acetone-d6): 8.32 (d, 1H), 8.14 (s, 1H), 7.66 (s, 1H), 7.54 (d, 1H), 6.73 (s, 1H), 2.74 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. customThe mixture obtained
  3. washwas washed (3×) with water
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe solid obtained
  6. customThe solid obtained
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4a5618ceb1404bb29a6b2729beb5665c
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…